Preparation of alpha-aminoalkylphenols

Abstract

Prepare novel α-aminoalkylphenols by contacting an α-alkenylphenol and an amine under reaction conditions.

What is claimed is: 
     
       1. A process comprising contacting an ortho- or para- α-alkenylphenol and ammonia or a primary or secondary amine under reaction conditions to form an α-aminoalkylphenol. 
     
     
       2. The process of claim 1 wherein the α-aminoalkylphenol is represented by the following formula: ##STR3## wherein R b  and R c  are independently H or lower alkyl; R and R a  are independently H, lower alkyl, or substituted lower alkyl; or R and R a  taken together are alkylene or heteroalkylene portions of a heterocycloalkyl moiety formed by R, R a , and the N atom and α carbon atom of the preceding formula; and the --OH moiety is in the ortho or para position relative to the aminoalkyl moiety. 
     
     
       3. The process of claim 2 wherein R b  is methyl, and R c  is H. 
     
     
       4. The process of claim 3 wherein R and R a  are H. 
     
     
       5. The process of claim 3 wherein R a  is lowre alkyl. 
     
     
       6. The process of claim 1 wherein the selectivity to the α-aminoalkylphenol is at least about 80 mole percent. 
     
     
       7. The process of claim 3 wherein the hydroxyl moiety is in the para position relative to the aminoalkyl moiety. 
     
     
       8. The process of claim 1 wherein the amine comprises ammonia or hydroxylamine. 
     
     
       9. The process of claim 1 wherein the α-aminoalkyl phenol is represented by the following formula: ##STR4## wherein R b  and R c  are independently H or lower alkyl; R is H, lower alkyl or substituted lower alkyl, and R a  can be R, --NH 2 , --CH 2  CH 2  OH, --OH or --CH 2  CH 2  NH 2 , or R and R a  taken together can be ##STR5## 
     
     
       10. The process of claim 1 wherein the amine is a polyamine. 
     
     
       11. A process comprising contacting an ortho- or para- α-alkenylphenol and ammonia or a primary or secondary amine at a temperature of from about 0° C. to about 100° C. and under such other reaction conditions that an α-aminoalkylphenol selectively is produced. 
     
     
       12. The process of claim 11 wherein the contacting is in the presence of an inert reaction medium. 
     
     
       13. The process of claim 11 wherein the selectivity to the α-aminoalkylphenol is at least about 80 mole percent. 
     
     
       14. The process of claim 11 wherein the selectivity to the α-aminoalkylphenol is at least about 90 mole percent. 
     
     
       15. The process of claim 11 wherein the temperature is from about 20° C. to about 70° C. 
     
     
       16. The process of claim 11 wherein the α-alkenylphenol is represented generally by the formula: ##STR6## wherein R b  and R c  are independently H or lower alkyl; and wherein the hydroxy substituent is ortho or para to the alkenyl substituent. 
     
     
       17. The process of claim 11 wherein the amine is ammonia, 1,2,-diaminoethane, n-butylamine or hydroxylamine. 
     
     
       18. The process of claim 16 wherein R b  is methyl and R c  is H. 
     
     
       19. A process comprising contacting ammonia or hydroxylamine with p-isopropenylphenol under reaction conditions to selectively produce 2-amino-2-(4-hydroxyphenyl)propane or N-[1-methyl-1-(4-hydroxyphenyl)ethyl]-hydroxylamine. 
     
     
       20. The process of claim 19 wherein the contacting temperature is from about 0° C. to about 100° C.